


those gamblers' blues

by madameofmusic



Series: St. Knight's Infirmary [1]
Category: Check Please! (Webcomic)
Genre: 1920s AU, Gen, Prohibition Era, speakeasy au
Language: English
Status: Completed
Published: 2018-03-27
Updated: 2018-03-27
Packaged: 2019-04-08 18:09:51
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,469
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14111091
Author URL: https://archiveofourown.org/users/madameofmusic/pseuds/madameofmusic
Summary: Dex is a bootlegger working for one B. "Shitty" Knight.





	those gamblers' blues

**Author's Note:**

> This only exists because of Hugh Laurie's cover of "St. James Infirmary." Title is from the same!
> 
> Part of something (eventually) longer.

Dex has been sitting at the docks for almost an hour now, and he’s starting to get a bit antsy. The cold, bay wind is biting through his thin cotton jacket, making the freckled skin underneath go numb. The fishing boat rocks underneath him as he shifts, leaning out over the railing to squint into the dark, cloudless night.

Knight’s never been this late before. In fact, Knight’s never been late at all, period.

Right as Dex is considering calling off their weekly exchange and phoning Knight later on in the week, he hears the rumble-engine of Knight’s Austin twenty.

The car comes to a stop next to Dex’s boat, the pier creaking under its weight. “You’re late,” Dex says as Knight swings open the door.

The person who steps out, though, isn’t Knight. He’s taller, and with the headlights from the car shining in Dex’s eyes, his face is obscured.

Dex’s hand settles on top of the gun at his hip. If it’s a cop, he’ll play it off like he and Knight had discussed when they made this deal last fall. If it’s a mobster, well. It wouldn’t be the first time Dex’d had to use his Beretta.

“Knight sent me,” the man calls out, turning the engine off and shutting the engine off. The relative quiet of the January night settles over them again as Dex looks him up and down.

“Knight doesn’t have errand boys.”

The stranger’s eyes narrow, lips curling with distaste at Dex’s words. “He does now.” The stranger steps closer, and Dex pulls out the pistol, but leaves it pointing at the ground, making his intentions as clear as they can be. “Put the gun away, and I’ll show you his note.”

Dex licks his lips, and re-holsters the gun. “Fine.”

The stranger walks closer, a piece of paper held in his hand. Dex takes it from his outstretched fingers, and pretends to read it over.

Dex, the son of farmers, doesn’t know how to read. It’s not something anyone else needs to know, not when his only job is bootlegging and catching his own dinners. _Reading,_ he frequently says to his little sister, _is for the rich._

Catherine, benefiting from her status as a woman and the money her rich husband brings in, has the benefit of books and time to make fun of him for not knowing his alphabet. He tries not to let it get to him.

He drops the note into the harbor, and both he and the stranger watch as the soft waves push it underneath the boat and away. “I’m coming with you.”

The stranger steps back, dark skin catching in the moonlight and setting his figure alight in profile. He seems familiar, somehow, but Dex can’t place him. “Why?” He asks, almost a whine to his voice.

Dex narrows his eyes, not that the stranger can probably see that in the dark, and frowns. “Because I don’t know if I can trust you for sure, and I’m not giving up this much liquor without a fight.”

He also wants to make sure the haul is going to Knight, and not to the cops. The boat isn’t his, but one of his uncle’s fleet, and there’s no way in hell he’s letting there even be a chance his own illicit activities would be traced back to his family. Just because this guy shows up in the same kind of car Knight drives (a very expensive, uniquely colored one) claiming to be working for him doesn’t mean he’s not a narc. Dex has heard about more complicated stings before.

The stranger huffs. “The note—”

“Don’t care.” Dex ducks into the main cabin of the boat, and comes back dragging the first crate. The bottles, tucked carefully between sheets of old newspaper, don’t even clink inside. If questioned, the print on the side and the weight of the crates (minus the obvious sounds of glass) would allow Dex to claim that he’s transporting catch. It’s not an airtight plan, but its the best he’s got.

The stranger takes the crate with a soft _whoof_ of air as Dex drops it in his arms, and goes to put it in Knight’s car as Dex grabs the next one. They assembly-line their way through half a dozen crates, enough for two weeks at the Haus, before Dex locks the door to the cabin and hops onto the pier.

The stranger shuts the hatch, and turns the car on, giving Dex barely any time to strap in before he’s peeling away from the docks and back towards town.

“Drive more conspicuously, will ya?” Dex hisses, hands scrabbling for purchase on the inside of the door as the car rumbles and bumps along the rough stone streets back to the Haus.

“We’re already late,” The stranger replies, picking up even more speed. Dex can feel the car’s engine shaking the chassis, and though he’s spent his whole life on rickety boats and ricketier piers, he’s a little afraid that the car’s going to shake apart at the bolts.

Dex grits his teeth and says nothing else for the rest of the ride, one hand white-knuckling the edge of the seat, and the other tapping an anxious rhythm on his knee.

The stranger finally slows as they approach the Haus, and pulls up behind, into the concealed garage Knight had had built a few years back, right before the eighteenth went through and fucked him over. Bitty pulls shut the doors behind him.

Knight was standing by the doorway between the garage and the storeroom. “You’re late, Nurse.”

The man, Nurse, parks the car and shuts it off. “I wouldn’t have been if you’d given me better directions.” He and Knight shake hands, and Dex can tell Knight’s grinning, even from here.

He gets out, and Knight’s grin grows even wider. “Dex! Finally decided to join us, have you?”

“You know I don’t drink, Knight,” Dex says, though he accepts the man’s handshake with a warm smile.

Dex’s mother, a staunch Catholic and prohibitionist, though dead for nearly a decade now, had been alive just long enough to put the fear of God and drink into Dex and his siblings.

However, just because he didn’t drink didn’t mean he was dumb enough to turn down good money, even with only Knight as his client.

“I’ve told you, Dexy, call me Shitty,” Knight says, clapping him on his shoulder and letting him go.

Dex’s nose crinkles at the word, but doesn’t respond, unwilling to get in another common argument between himself and Knight. “Profane words,” his mother used to say, “are the products of the weak-willed,” and though Dex doesn’t necessarily agree, the words Knight and his employees use with ease still feel dry and heavy on his tongue.

“Knight, is… he,” Dex says, pointing over his shoulder at Nurse. “Picking up your liquor every week?”

Knight nods. “New worker. I gotta start staying here more.” Knight’s eyes flick between the dark street behind the bar and the door, soft sounds of drinking and gambling filtering through the door. “The beat’s started working its way down here.”

Dex swallows, the prospect of losing his best-paying (well, really _only_ ) customer sinking a stone in his stomach. The money he’s been making, saving, well. It’ll only go so far. God forbid something awful happen to the banks, like his mama’s always saying will, otherwise the entire Poindexter clan will be one step from begging yet again. “Alright. I’ll look out for him next week.”

Knight nods, and claps him on the shoulder. “Let me drive you back.”

Dex shakes his head. “I can take the streetcar.”

Knight frowns. “You’ll have to walk to the docks. Streetcar doesn’t go that far.”

Dex shrugs, not willing to voice the fear he has of being out this late at night with a known rabble-rouser, and tanking both of them. He’d rather walk. “I’ve got Bess,” he says, patting the pistol at his hip.

Knight sighs, still frowning, but nods. “See you next week. Maybe come hang out.”

Dex smiles ruefully, both of them knowing there’s little chance he’ll do that. “I will, Knight.”

Dex catches the last car to the edges of the city, and spends his walk whistling under his breath an old tune his mama taught him, trying not to think too much about the shadows on the edges of alleys and under awnings. This city’s been safer since the last takeover swept most of the petty criminals back across the river, but one can never be too wary.

His boat, rickety and falling apart as she is, is a welcome sight of safety. He climbs on and pushes off the dock, letting the city lights blink out behind him as he motors away, back towards home.

**Author's Note:**

> Big big shout out to Linnea, who, when I said "hey I want to write a thing but there's no it would work for check please," basically went "the hell it wouldn't" and convinced me to write it, along with cheering me on/helping me plan/being a wonderful human being in general. Find her here: [(x) ](https://rushingsnowy.tumblr.com/)
> 
> Another big shout-out (and bigger thank you) to JustLookFrightened on tumblr, who went through and made sure all my typos were no longer typos. Find them here: [(x) ](https://justlookfrightened.tumblr.com/)
> 
> Final thank you to the omgcp fic writers discord. Bless y'all. 
> 
> Find me on [tumblr ](https://whiskeytangofrogman.tumblr.com/)


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